Diisopropylethylamine → N-((1-hydroxy-1H-spiro[benzo[c][1,2]oxaborole-3,1'-cyclopentan]-6-yl)methyl)-5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxamide

Participants

Reaction Steps

A solution of 5-(5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)indolizine-8-carboxylic acid (0.67 mmol) and DIPEA (346 mg, 2.68 mmol) in DMF (10 mL) can be stirred at rt for 5 min and then HATU (510 mg, 1.34 mmol) can be added. The mixture can be stirred for 10 min prior to the addition of 6-(aminomethyl)-1H-spiro[benzo[c][1,2]oxa-borole-3,1′-cyclo-pentan]-1-ol hydrochloride (202 mg, 0.80 mmol). And the resulting mixture can be stirred at rt overnight. It can be then concentrated under vacuum, and the residue can be partitioned between 1N HCl and ethyl acetate. The organic layer separated can be concentrated under vacuum, and the residue can be purified on column chromatography and prep-HPLC to provide the title product.

Provenance & Evidence